Biosynthesis of Riboflavin. A Simple Synthesis of the Substrate and Product of the Pyrimidine Deaminase and of Structural Analogs
نویسنده
چکیده
2-Amino-5-nitro-6-ribitylamino-4(3H)-pyrimidinone (7) was phosphorylated with chlorophosphoric acid yielding an isomer mixture containing about 63% of the 5'-phosphate 7a together with other monophosphates and bisphosphates of 7. Preparative HPLC afforded pure 7a. Catalytic hydrogenation of 7a yields the labile substrate of pyrimidine deaminase, 2,5-diamino-6-ribitylamino-4(3H)-pyrimidinone 5'-phosphate (2a). The product of the enzyme, 5-amino-6-ribitylamino-2,4(l H.3H)-pyrimidinedione 5'-phosphate (4a), can be obtained from 5-nitro-6-ribitylamino-2,4(lH,3H)-pyrimidinedione (8) by an analogous procedure. The 3'and 4'-monophosphates of 2,5-diamino-6-ribitylamino-2,4(lH,3H)-pyrimidinedione are not substrates for the deaminase. 5'-Phosphates of a variety of ribityl-substituted pyrimidines and pteridines could also be obtained by phosphorylation with chlorophosphoric acid without the use of protecting groups.
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